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The main two advantages of separate stylesheets referenced by CC for IE:
1. It makes it easier to chuck the rules when you’re ready to retire support for a particular IE
2. It’s a place to stick those proprietary IE rules (like filter: alpha(opacity=80);) that will keep CSS from validating.
That said, I find it easier to keep all my hacks, er patches, in one CSS file. I think I treat them different than the average joe. I use the * html hacks for win IE lt 7 and *+html hacks for IE 7 (this would reduce your first IE CSS patch example in the article by the same amount as a separate stylesheet). Most importantly, these days I tend to group them in one spot in the stylesheet. All * html hacks coming at the end of my stylesheet for example. This way, they’re in the same consistent spot if I need to root them out.
It’s no less cumbersome than having to edit them in a separate file, but I’ve reduced the number of http request.